Hi there...
I have the same struggles myself and found that the best way to find out is to get out there and explore. I do know that the Daley Ranch and Elfin Forest Recreational Reserve are both jogger stroller friendly (as long as it has bike tires and not hard tires). You might have to do a little maneuvering in spots with the jogger, but it's a great workout pushing those things along on a hike.
As well, most places are dog friendly if you keep them on a 6 foot leash, but there are definitely no dogs in Cuyamaca except for the Cuyamaca Fire Trail.
One thing to look into is a backpack to carry your child in. I dont know the weight limits and all as my son is 10 months and has plenty of room to grow; but the pack is awesome!! Not only can you store stuff in compartments, but you can also enjoy the hike without pushing and maneuvering.
I'll share trails as I experience them, and know that all my hiking is done with my dog and son in tote.
Joe~